In today’s edition, we explore why the majority of buyers say salespeople don’t understand their business, and how that’s costing you sales. We dig into how tailored conversations build trust, relevance, and ultimately win more deals.

Hello Reader,

Imagine you’re buying a suit for an important event, and you have two options.

1. You can get a tailored suit, meticulously crafted to your exact measurements. Every seam fits perfectly, the shoulders align just right, and the sleeves fall exactly where they should. It feels comfortable, looks sharp, and you know it was made just for you.
2. The other option is off-the-rack. It’s faster to grab, cheaper, and “close enough” most of the time. But it never fits right. The shoulders might be too wide, the sleeves too long, or the waist too loose. It feels like a compromise, and you can tell it wasn’t made with you in mind.

It was a general “one-size-should-fit-all-around-this-height-and-size” solution.

The question in that scenario would be, do you go tailored… or do you settle?

The reality is, if you have the money, you’ll never settle.

Now think about your prospects who are ready to invest in the products or services you provide.

Why should they settle?

This is exactly how buyers feel about most salespeople. Buyers regularly feel that salespeople don’t understand them, their needs, or goals.

They hear pitches that feel generic, scripted, and off-the-shelf. Like an off-the-rack suit, it just doesn’t fit their unique needs or challenges.

And here’s the tough truth: When buyers feel misunderstood, they don’t buy.

Why tailored sales conversations win

1. Relevance builds trust: When you demonstrate that you get their specific business, industry, and pain points, buyers relax. They’re more likely to engage because they feel you’re speaking directly to them, not just reading a script.
2. It shows respect: Taking the time to tailor your approach says you respect the buyer’s time and challenges. It signals you’re serious about helping… not just selling.
3. Tailoring uncovers real problems and opportunities: When you understand the nuances of their business, you can position your solution in ways that matter to them. Not just features or benefits on a generic list.

How to tailor your sales approach effectively

1. Research deeply before the conversation: Know their industry, competitors, recent news, and typical challenges. LinkedIn, company websites, and industry reports are your friend here.
2. Ask open-ended questions early: Don’t jump to pitch. Start by learning their goals, frustrations, and priorities. This builds rapport and uncovers exactly what they need.
3. Use their language: Mirror their terminology and way of talking about their business. This subtle connection makes your pitch feel natural and relevant.
4. Customise your solution’s value: Don’t rattle off a generic product list. Tailor your value proposition to address their unique problems and desired outcomes.

And here some “off-the-rack” mistakes to avoid:

• Leading with features instead of benefits tailored to their context
• Using boilerplate emails or scripts without personalisation
• Failing to listen and adjust during calls or meetings

Remember that if you want buyers to say yes, it’s crucial to avoid being the “off-the-rack” and instead becoming a tailored one. Tailor your approach so every buyer feels it was made just for them.

Your next deal could hinge on this small but powerful shift.

Here’s to tailoring your success,

James

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